


The Set Up

by anniesardors



Category: Chicago PD (TV)
Genre: First Kiss, Flirting, Fluff, Ice Skating
Language: English
Status: Completed
Published: 2021-01-01
Updated: 2021-01-01
Packaged: 2021-03-11 02:20:22
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,454
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28487448
Author URL: https://archiveofourown.org/users/anniesardors/pseuds/anniesardors
Summary: When Jay and Hailey are stood up by their friends at the annual winter festival, they decided to enjoy themselves with some ice skating and winter festivities. Heavy flirting and fluff ensues.Upstead oneshot
Relationships: Jay Halstead & Hailey Upton, Jay Halstead/Hailey Upton
Comments: 1
Kudos: 86





	The Set Up

**Author's Note:**

> Hello all! Here is a fluffy little one-shot because when can we not use some upstead fluff! Please let me know what you think! Your kind words and support mean so much :)

It's been a long week and it's only Tuesday. The Intelligence unit has caught a murder case that seems like it will never end and they are all already tired from the early mornings and late nights. They can't seem to catch a break and they are all starting to get frustrated.

It's 10:43 pm on Tuesday when they are all finally leaving the unit, dead on their feet. They are making their way out to the parking lot when Vanessa says "I have an idea."

They all look at the young officer and Hailey swears she has too much energy after being at work all day, but they all secretly love it.

"Friday is the last day of the winter festival," Vanessa says. "We should go. We can do ice skating and drink all of the specialty alcohols they have at the different booths."

"Hate to break it to you," Adam says. "But there's a chance we will still be working this case Friday night."

Vanessa shrugs. "And if we are, then we don't go. But if we somehow end up wrapping this case before then, we at least have something to look forward to."

She had a point, and at least their celebratory plans would not be spending another night at Molly's. Despite how much they loved the little bar and all it stood for, they were there more often than not and all stated on several occasions they needed to branch out.

"I'm in," Kim says. "It could be fun."

"I'm down," Kevin adds. "I'll show you all my mad ice skating skills."

"Oh bro it's on," Adam says. "I'll destroy you."

They all laugh and as they make their way to their respective rides home for the night, Hailey says, "I guess it's settled."

They all look to Jay, knowing he would be the hardest to convince. He leans against his truck and sighs. "Fine. But if one of us breaks a bone, Voight will kill us."

\--------------------------------------------------------

It's Thursday night (well, actually early Friday morning, but who is keeping track) when they find themselves covered in dirt and a little bit of blood, but they have caught their murder and they can all let out a relieved sigh. They are all tired when they return to work late Friday morning and they know that it will be an easy day of paperwork. The weight of the week is heavy on them and Hailey thinks a few times, someone will speak up and suggest they cancel their plans for tonight, but then they all look at Vanessa and see how excited she is. They can drink an extra cup of coffee in order to have enough energy for tonight because it means so much to her.

When they are in the locker room at the end of the day, Jay offers to drive Hailey and Vanessa, citing the fact that it does not make sense to bring multiple cars when parking downtown is probably going to be a nightmare. Hailey is about to respond yes when Vanessa cuts her off.

"I'm actually going to go home with Kim. She said she'll drive me. That okay?" Vanessa looks at Hailey. Hailey nods slowly and before she can question further, Vanessa happily shuts her locker and says. "I'll see you guys there!"

Hailey looks back to Jay. "That weird to you too?"

He gives out a small laugh. "It's Vanessa. I wouldn't think much of it." He pauses, before saying. "The offer still stands. Want me to drive you?"

She has to stop herself from smiling because it's just an offer to drive her. It's sensible and good for the environment she tells herself. It's most certainly not anything more (but the beating of her heart and the way her cheeks slightly redden tell her that her heart and her brain are not quite in sync.)

Hailey nods. "Yeah. I'm going to run home and change. Pick me up at 6?"

"You got it."

\--------------------------------------------------------

When Jay and Hailey park, it's 6:27 pm. The gang agreed to meet at the ice rink at 6:30, so the partners jump out of his truck and made their way to find their friends. Hailey sends a text in their group chat to let their friends know they are there. Their walk to the rink is quiet, with the exception of when one of them points out a funny booth that is set up at the winter festival or they make a joke about how none of them are going to be able to successfully ice skate.

Jay and Hailey stand outside the ice rink and watch people ice skate for a few minutes while waiting for their friends. Hailey checks her phone every so often, but there are no new messages on her phone.

"Maybe they are trying to find a spot to park," Jay suggests when he sees Hailey check her phone for what must be the fifteenth time.

"We definitely should have all driven together." She laughs and pulls her winter jacket a bit tighter over her chest. She had a knit sweater on and her red winter jacket, along with a white beanie, but she can still feel the cold Chicago air run through her.

His gaze is still on the skaters in front of them when he calmly says. "Yeah, but then we wouldn't get a few minutes alone without our idiot coworkers."

Her cheeks burn and it's not from the wind. She wants to make a flirty comment, but she can't bring herself to, so she simply says, "There are not all idiots."

"No, they're not. They're pretty great." He agrees with her. "But I bet you a drink that Adam falls on his ass by the end of the night."

"Make it a drink and a pizza and you got yourself a deal."

They laugh and wait a few more minutes for their friends, but still, there is nothing. When it's 6:45 pm, both of their police senses are tingling because they have been conditioned to assume the worst. Hailey finally calls Vanessa, who picks up on the third ring.

"Hey, Hailey." By the tone in the young officer's voice, Hailey can tell she is nervous.

"Everything okay? Where are you guys?"

"Everything is fine." Vanessa is quick to say. "I'm at Kim's and the guys are with us. We'll be there later, sorry."

"What happened?"

Vanessa sighs. "It's a long story. Kim got the time wrong and then Kevin needs gas in his car and….we'll try to be there later."

"What do you mean try?" Hailey says with a tad of frustration and Jay gives her a questioning look. She shakes her head and puts up a hand, signaling him to wait.

"I'll keep you updated. Sorry, Hailey. Have a good time with Jay." Hailey can hear the muffled voices of her coworkers in the background and she just sighs.

"Yeah. See you guys later."

She groans and looks at Jay. "I don't think they're coming."

"What? This was Vanessa's idea."

"I know," Hailey says. "They're all at Kim's place and Vanessa said something about Kim forgetting what time we said we would meet and they're running late and-"

"So, maybe we will see them, maybe we won't." Jay finishes her sentence.

"Exactly." She lets out a sigh and she can see her breath in the air. "We can leave if you want."

"We don't have to go." He states. "Just because they bailed on us doesn't mean we can't have a good time."

Hailey raises an eyebrow at him. "You want to go ice skating?"

"I'll have you know, I'm a master ice skater. It's one of my many talents." He shoots a wink at her and Hailey knows she is in for a long night.

\--------------------------------------------------------

As it turns out, Jay is not a master ice skater. His skills resemble that of a toddler who is just learning how to walk. He falls several times on the ice, struggling to stand or to move a few inches without falling flat on his face. Hailey watches for a few minutes, laughing at her partner before she finally takes pity and grabs his hand and drags him along with her.

"I was just faking back there." He tells her.

"Sure, keep telling yourself that." She rolls her eyes, but thankfully he can't see, his eyes set on the ice ahead.

He leans a bit closer to her and whispers, "I always knew you wanted to hold my hand."

"I'll let go of you." She warns and he straightens up a bit in fear. She lets out a loud laugh before saying, "So ice skating is one of your many talents, huh?"

"Oh, don't worry, I am much better at other things." He says somewhat suggestively and she wants to smack him, but she knows he will fall right over if she lets go of him for a second.

"You are such a flirt, you know that?" She can still feel his hand in hers and she is thankful she is wearing gloves and he can't tell by her hand how nervous she is.

"Only with you." He says and she rolls her eyes yet again.

"Yeah, no. Pretty sure I've seen you flirt with like half of Chicago."

He doesn't answer at first and she glances over at him and sees a serious, yet gentle look on his face. "Well…" He finally says. "I only mean it with you."

She smiles and she has to make an effort to not let it take over her whole face. She is clearly failing because his smile lights up too. It's a dangerous line they are walking. They are both acutely aware of the feelings they both harbor for the other, but neither has taken that leap yet. It's a difficult position they are in, being partners, and they have a difficult and at times dangerous, job. They have so many things stacked against them, but during moments like this one, ice skating, hand in hand, flirting quietly, they both think maybe they have more going for them than they previously believed.

Hailey does not say anything and just continues to skate, pulling his hand along with her. After a few moments, he finally breaks the silence. "So, you going to tell me where you learned to skate?

"There was this pond a couple of blocks down from my house when I was a kid." She says quietly. "When the ice would freeze, a bunch of neighborhood kids would go down and we would play hockey."

Jay chuckles at the thought of a small Hailey wielding a hockey stick much too large for her, most certainly dominating the game. "You mean to tell me my partner is also a hockey star?"

She smiles and she does not know why, but she is starting to feel more confident. "Oh yeah." She lets go of his hand and turns herself around so she is standing in front of him, skating backward. "I have many talents." She says cheekily, before skating off.

\--------------------------------------------------------

They skate for a while after that. Jay is initially caught off guard after Hailey's "talents" comment and almost falls flat on his face, but she grabs his elbow and joins their hands again. She tells him it's just because she does not want him to break his arm because then she would have to train a new partner, but neither of them buys the excuse.

Their flirtation grows bolder throughout the night. They are both becoming more comfortable and confident and trying to outdo the other. Hailey likes this stage of things and she is secretly happy the rest of their friends have not shown up yet.

Around 8 o'clock, they find themselves wandering around the winter festival, both sipping on hot chocolate and sharing some carnival deep-fried pastry that they most certainly should not be eating. They are laughing about some old story Jay told her about him and Will from when they were kids and she can't think of the last time she was this happy. She likes this happy feeling in her stomach and she is feeling bold, so she changes the topic slightly.

"It's kinda weird that Kim mixed up the times, right?" She says. "That's pretty unlike her."

"Yeah. And I know for a fact Kev has enough gas to get them here and back? I was with him when he filled up his tank the other day."

She hums and takes a sip of her hot chocolate before saying, "You realize they purposely didn't come, right?"

"Oh, one hundred percent. There is a reason none of them have made detective yet. They're really not that discreet." They both laugh at his joke because while their friends were incredibly talented police officers and some of the best this city had to offer, they were really quite obvious about their mission tonight.

"This was definitely Vanessa's idea," Hailey tells him. "Every time you leave my place she makes a comment."

"Kev was giving me a hard time about us the other day," Jay adds as if it is common knowledge. "And Kim likes to tell me about once a week that I need to get my head out of my ass."

Hailey laughs because that sounds like Kim. "Maybe they're the ones who should be detectives because they clearly see what's going on here when we don't."

"Who said we don't see it?" Jay asks and when she looks up at him, he looks calm. He is wearing a black beanie, which slightly covers his forehead, and his eyes glance between her and his drink. He hands her the final piece of their desert and throws away the wrapper, acting as if they were having any other normal conversation.

"So we see it, we just don't do anything about it?" Hailey clarifies.

He shrugs. "Well, not yet at least. I mean, this is practically a date, so maybe I'll finally get the courage to kiss you when I drop you off at home."

Damn him and his boldness. Her cheeks turn a bright shade of red and there is a small smile on her lips. She feels a strange mixture of confidence and nerves, knowing that they are finally having that conversation and she was certainly not expecting this when they decided to come to the winter festival.

"Well, I don't know if I would call this a date." She teases. "I mean our friends kinda tricked us into coming here."

He nods, taking the last sip of his hot chocolate before finding a trash can to throw up the cup. He reaches out for Hailey's cup, knowing she finished hers several minutes ago and has just been holding the cup. He throws away their garbage and they continue walking.

"So, you saying you don't want to kiss me?" He cheekily asks and when she sees the smug smile he is sporting, she can't decide if she wants to smack it away or if she wants to just kiss him now.

"That's not what I said. Just saying, I'm not counting this as our first date. You're gonna have to ask me out"

He stops walking for a moment and just looks at her and she thinks he is going to ask her out here, but he quietly says "Noted" before grabbing her hand and pulling her along as they continue to walk through the festival.

\--------------------------------------------------------

By the time they have walked through the whole festival, it is 8:45 pm. They are making their way back to his car, still walking slowly and still holding hands. Jay has made a few more jokes about this being a date and Hailey continues to tell him to keep wishing (although they both know there is a pretty good chance she'll kiss him before he gets the chance to kiss her goodnight when he drops her off, but neither says anything.)

They are close to the parking lot when they hear voices that pull them out of their little bubble. "Hailey! Jay!" A voice yells and they scan the festival and see Vanessa waving at them, with Kevin, Adam, and Kim standing behind her. Hailey becomes incredibly aware of how close she is standing to Jay and the fact that her hand is still in his. She tentatively lets go of him and they make their way to their friends.

"I thought you guys weren't coming." Jay tries to sound casual as he questions them.

Vanessa has an innocent look on her face, almost as if she did orchestrate this whole thing and like she did not just see the two partners holding hands. "I texted Hailey like an hour ago that we were on our way."

"Sorry," Hailey says. "I must have missed your text."

"Obviously." Vanessa teases.

"You guys missed ice skating," Jay says, trying to divert the attention of the group.

"Oh don't worry," Kevin says. "We all came here last week while you two were at Molly's. We did ice skating and Adam made a total fool of himself."

They all laugh and Hailey looks at their friends. "Why didn't you tell us about last week? We would have come with you."

Vanessa shrugs. "You two already had plans. That's why we figured we should all come back today. And by the looks of it, it seems like that was a good idea."

The obvious meaning of Vanessa's comment is not lost on anyone. Jay smirks a bit and says, "Yeah until you all forgot about us."

"Oh don't worry man." Adam pipes in. "We'll all watch the Blackhawks game at my place tomorrow. I'll bring extra beer to make it up to you guys."

Hailey nods, before saying, "Is there anything you guys still want to go see? We'll join you."

Vanessa smiles and her and Kim lead the way back into the festival.

\--------------------------------------------------------

It's a little after 10:00 pm by the time Jay pulls up at Hailey's place. The gang spent a little over an hour wandering around the winter festival, maundering in and out of different pop-up shops and stopping to play a few of the carnival games that were set up outside. Eventually, the strong Chicago winds were too much for them to take and they called it a night.

Vanessa went home with Jay and Hailey, sitting in the back seat of his truck. They chatted about the festival, about different cases, and about anything and everything. When Jay finally parks outside of the girls' house, Vanessa bids him goodnight and Hailey tells her roommate that she will be inside in a few minutes.

"Well, that was a night," Hailey says when they are alone, resting her head against the back of her seat.

He hums and turns slightly in his seat so he is facing her. "You know, if I remember correctly, a bet was made tonight?"

"Yeah?"

"I believe I bet you a drink that Adam would fall on his ass while ice skating. I think the fact that he fell last week still counts."

Hailey laughs. "If we are going by that logic, I think you owe me a drink and a pizza."

"Good point." He chuckles softly.

"You know," She starts, keeping her head on the seat, but turning it so she can see him, "you could just ask me out on a date and we could go get pizza and that would kill two birds with one stone."

He smiles. "I could do that, but I don't think it's very romantic to have our first date be because of a bet."

"I'll tell you what, then," She turns in her body seat to fully face him, resting her hands in her lap. "I'll ask you out and we'll just save the pizza from the bet for a rainy day. How's that sound?"

"Sounds like you're a genius." He has a dopey smile on his face that she does not think she has ever seen, but she believes she would like to see more of. "One question though?"

"What's that?" Hailey says.

"Say I didn't wait until after the first date to kiss you? How mad would you be?"

She doesn't answer at first, just gives him a sweet smile and leans over the center console to press her lips to him. It's a short kiss, but it's sweet and it's meaningful. It's something to grow upon in the future. When she pulls back and looks up at him, she just whispers, "I don't think I'd be all that mad."

"Oh good." He says before kissing her again.

Nope. Not mad at all.


End file.
